DE2719733A1 - SCHAEDLING INHIBITOR - Google Patents

Abstract

Insecticidal composition containing, as active ingredient, a compound of the formula I <IMAGE> in which either R1 or R2 in each case denote hydrogen or methyl and R3 denotes phenyl or R1 and R2 simultaneously denote hydrogen and R3 denotes p-chlorophenyl, p-methylphenyl or o-methylphenyl, and their tautomers.

Description

Pesticides

The present invention relates to a pesticide containing as active component a 5-phenylcarbamoylbarbituric acid and its Use for pest control.

The 5-phenylcarbamoylbarbituric acids contained in the agent according to the invention correspond to formula 1 wherein either i) R1 and R2 each represent a hydrogen atom or a methyl group and R3 represents a phenyl group; or ii) R1 and R2 simultaneously represent a hydrogen atom and pure p-chlorophenyl, p-methylphenyl or o-methylphenyl groups and their tautomers.

The compounds of formula I, i.e. 5-phenylcarbamoyl-barbituric acid; 5-phenylcarbamoyl-1-methyl-barbituric acid; 5-phenylcarbamoyl-1,3-dimethyl-barbituric acid; 5- (4-chlorophenyl) carbamoyl barbituric acid; 5- (4-methylphenyl) carbamoyl barbituric acid; and 5- (2-methylphenyl) carbamoylbarbituric acid are known [cf. "Acta. Pol. Pharm." 24 (6): 647-649 (1967); "Diss. Pharm. Pharmacol." 18 (1): 31-50 (1966); Japanese Patent No. 1408 / '64); and "Chem. Ber." 98, 131-139 (1965)] and are after per se known methods obtained by e.g.

a) an ester of the formula II with an aniline of the formula III reacts R3-NH2 (III); b) a compound of the formula IV can react with an isocyanate of the formula V R3-N = CO (V); or that c) a compound of the above formula IV is treated with an azide of the formula VI R3-CO-N3 (VI); where in formulas II to VI R1 to R3 have the meanings already given under formula I and R4 stands for a C1-C4-alkyl group.

Preferably processes (a) and (c) are carried out at one reaction temperature between 100 and 200 C and the process (b) at a reaction temperature between Pre-minted O and 200 C. The reactions can take place at normal or increased pressure, if necessary in a solvent or diluent which is inert towards the reactants and optionally carried out in the presence of a base, As a solution or Diluents for these reactions are e.g. Ether and ethereal compounds, such as dipropyl ether, dioxane, dimethoxyethane and tetrahydrofuran: amides such as N, N-di-alkylated Carboxamide; aliphatic aromatic and halogenated hydrocarbons, especially toluene, xylenes and chlorobenzene; Nitriles such as acetonitrile; DMS0 and Ketones such as acetone and methyl ethyl ketone.

The bases used include, in particular, tertiary amines, the triethylamine, dimethylaniline, Pyridine, picolines and lutidines, as well as hydroxides, oxides, carbonates and bicarbonates of alkali and alkaline earth metals as well as alkali metal alcohols (-e wi z .13.

Potassium t, butylate and sodium methylate are considered.

According to the present invention it has now surprisingly been found that the compounds of the formula I have excellent insecticidal activity own. In particular, the compounds of the formula I have a very beneficial effect against insects which are harmful to plants and animals and can e.g.

according to the invention for combating insects of the families: Acrididae, Blattidae, Gryllidae, Gryllotalpidae, Tettigoniidae, Cimicidae, Pyrrhocoridae, Reduviidae, Aphididae, Delphacidae, Diaspididae, Pseudococcidae, Chrysomelidae, Coccinellidae, Bruchidae, Scarabaeidae, Dermestididae, Tenebrionidae, Curculionidae, Tineidae, Noctuidae, Lymantriidae, Pyralidae, Galleridae, Culicidae, Tipulidae, Stomoxydae, Muscidae, Calliphoridae, Trypetidae and Pucilidae can be used.

Above all, however, the compounds of formula 1 are suitable for combating of ectoparasitic insects such as Lucilia sericata and insects that live in the Areas of hygiene and stock protection are detrimental.

The insecticidal effect can be increased by adding other insecticides and / or widen acaricides considerably and adapt to the given circumstances.

Examples of suitable additives are: organic phosphorus compounds; Nitrophenols and their derivatives; Formamidine; ureas; pyrethrin-like compounds; Carbamates and chlorinated hydrocarbons, the agents according to the invention are produced in a manner known per se by intimate mixing and / or grinding of active ingredients of the formula I with the suitable carriers, optionally with the addition of opposite dispersants or solvents that are inert to the active ingredients.

The active ingredients can be in the following working-up forms and are used: Solid forms of processing: dusts, grit and granulates (Coated granules, impregnation granules and homogeneous granules); Liquid processing forms: a) active ingredient concentrates dispersible in water: wettable powder, Pastes and emulsions; b) Solutions The content of active ingredient in those described above Average is between 0.1 to 95%, it should be mentioned that in the application from the aircraft or by means of other suitable application devices also higher Concentrations can be used.

The active ingredients of the formula I can, for example, be formulated as follows : Dusts: For the production of a) 5% and a) 2% dust the following substances are used: a) 5 parts of active ingredient, 95 parts of talc; b) 2 parts of active ingredient, 1 part of highly disperse silica, 97 parts of talc.

Each active ingredient is mixed with the carrier and ground.

Granules: The following are used to produce 5% granules Substances used: 5 parts of active ingredient, 0.25 parts of epichlorohydrin, 0.25 parts of cetyl polyglycol ether, 3.50 parts of polyethylene glycol, 91 parts of kaolin (grain size 0.3-0.8 mm).

The active substance is mixed with epichlorohydrin and 6 parts Dissolved acetone, then polyethylene glycol and cetyl polyglycol ether are added. The solution obtained in this way is sprayed onto kaolin and then the acetone evaporated in a vacuum.

Wettable powder: For the production of a) 40%, b) and c) 25% d) 10% fuel powder, the following ingredients are used: 40 Parts of active ingredient, 5 parts of sodium lignin sulfonic acid, 1 part of sodium dibutylnaphthalenesulfonic acid 54 parts of silica; b) 25 parts of active ingredient, 4.5 parts of calcium lignosulfonate, 1.9 Parts of champagne chalk / hydroxyethyl cellulose mixture (1: 1), 1.5 parts of sodium dibutyl naphthalene sulfonate, 19.5 parts of silica, 19.5 parts of Champagne chalk, 28.1 parts of kaolin; c) 25 parts Active ingredient 2.5 parts of isooctylphenoxy-polyethylene-ethanol, 1.7 parts of champagne chalk / hydroxyethyl cellulose mixture (1: 1), 8.3 parts of sodium aluminum silicate, 16.5 parts of kieselguhr, 46 parts of kaolin; d) 10 parts of active ingredient, 3 parts of a mixture of the sodium salts of saturated fatty alcohol sulfates, 5 parts of naphthalenesulfonic acid / formadelhyd condensate, 82 parts of kaolin; The active ingredients are intimately mixed with the aggregates in suitable mixers and adjusted to the appropriate Mill and roll grind. Spray powder is obtained, which becomes a suspension with water allow to dilute to the desired concentration.

Emulsifiable concentrates: For the production of a) 10% b) 25% and c) 50% emulsifiable concentrate, the following substances are used: a) 10 Parts of active ingredient, 3.4 parts of epoxidized vegetable oil, 3.4 parts of a combination emulsifier, consisting of fatty alcohol polyglycol ether and alkylaryl sulfonate - ("alcium-Salz, 40 Parts of dimethylformamide and 43.2 parts of xylene; b) 25 parts of active ingredient, 2.5 parts of epoxidized Vegetable oil, 10 parts of an alkylarysulfonate / fatty alcohol polyglycol ether mixture, 5 parts of dimethylformamide and 57.5 parts of xylene; c) 50 parts of active ingredient, 4.2 parts Tributylphenol polyglycol ether, 5.8 parts Ca-odecylbenzenesulfonate, 20 parts cyclohexanone, 20 parts of xylene.

Such concentrates can be diluted with water to produce emulsions the desired concentration can be produced.

Spray: For the production of a) 5% and b) 95% spray the following components are used; a) 5 parts of active ingredient, 1 part of epichlorohydrin, 94 parts of gasoline (Siedegrezen 160-1900C) 95 parts of active ingredient, 5 parts of epichlorohydrin the The following examples serve to explain the invention in greater detail: Example 1 Insecticidal feed poison effects: Spodoptera littoralis, Heliothis virescens and Leptinotarsa decemlineata.

Cotton plants and potato trees were treated with a 0.05% aqueous Active ingredient emulsion (obtained from a 10% emulsifiable concentrate) sprinkled.

After the covering had dried on, the cotton plants were each with Spodoptera littoralis or Heliothis virescens larvae (L3 stage) and the potato plants populated with Leptinotarsa decemlineata larvae (L3). An evaluation of the achieved They were killed after 2, 4, 8, 24 and 48 hours. The experiment was carried out at 24 ° C and 6ß% relative humidity carried out.

In the above experiment, compounds of the formula I showed a good feed poison effect against Spodoptera littoralis, Heliothis virescens and Leptinotarsa decemlineata larvae.

Claims (2)

Patent claims oil insecticidal agent containing a compound of formula I as active component wherein either i) R1 and R2 each represent a hydrogen atom or a methyl group and R3 represents a phenyl group; or ii) R1 and R2 simultaneously represent a hydrogen atom and R3 a p-chlorophenyl, p-methylphenyl or o-methylphenyl group, and their tautomers. 2. Use of a compound of the formula defined in claim 1 I to control insects.